Potassium Carbonate → HCID 69420618, compound

HRID 855997Notes

Reaction equation

HRID 855997 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:24][CH2:25][CH3:26]>CC(C)=O.C(OCC)(=O)C>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:24][CH2:25][CH3:26])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 336431-Iodopropane2×HCID 1380784-Hydroxy-4'-nitrobiphenyl

Product 1

HCID 69420618HCID 69420618, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-4′nitrobiphenyl in 5 ml acetone was added potassium carbonate (240 mg, 1.74 mmol) and 1-iodopropane (0.17 ml, 1.74 mmol). The reaction mixture was heated at reflux for 24 h. Additional potassium carbonate (240 mg, 1.74 mmol) and 1-iodopropane (0.17 ml, 1.74 mmol) was added and the reaction mixture was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and diluted with 30 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 25 ml water and 25 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel), eluting with 14:1 hexane/ethyl acetate to yield the title compound (0.267 g, 89% yield) MS: 258.3 (M−1)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 24 h
  5. washThe ethyl acetate solution was washed sequentially with 25 ml water and 25 ml brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel)
  9. washeluting with 14:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-5b5db85593b541c8898bb30278d9f8c9
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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